Ethyl levulinate → HCID 13920736, compound

HRID 477503Notes

Reaction equation

HRID 477503 reaction equation
[CH3:1][CH2:2][CH2:3][C:4]1[C:9]([OH:10])=[C:8]([C:11]([CH3:13])=[O:12])[CH:7]=[CH:6][C:5]=1[OH:14].N1CCCC1.[C:20]([O:27][CH2:28][CH3:29])(=[O:26])[CH2:21][CH2:22][C:23]([CH3:25])=O>C1(C)C=CC=CC=1>[OH:14][C:5]1[CH:6]=[CH:7][C:8]2[C:11](=[O:12])[CH2:13][C:23]([CH2:22][CH2:21][C:20]([O:27][CH2:28][CH3:29])=[O:26])([CH3:25])[O:10][C:9]=2[C:4]=1[CH2:3][CH2:2][CH3:1]

Participants

5

Reactant 3

HCID 10883Ethyl levulinateHCID 31268Pyrrolidine2×HCID 27751982',4'-Dihydroxy-3'-propylacetophenone

Product 1

HCID 13920736HCID 13920736, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 58.0 g (0.299 mole) of 2,4-dihydroxy-3-propylacetophenone and 29.5 ml (0.36 mole) of pyrrolidine in 250 ml of toluene was heated to reflux for three hours under a Dean-Stark trap. After cooling the mixture, 68.2 ml (0.48 mole) of ethyl levulinate was added and the mixture was refluxed for two hours. An additional 10 ml (0.12 mole) of pyrrolidine was added and the mixture was refluxed overnight under a Dean-Stark trap.

Workup

  1. temperatureto reflux for three hours under a Dean-Stark trap
  2. additionwas added
  3. temperaturethe mixture was refluxed for two hours
  4. temperaturethe mixture was refluxed overnight under a Dean-Stark trap

Sources & evidence

ORD record
ord-865ed420ecbc423e813c88c23a1f81e4
Source dataset
uspto-grants-1989_12
Patent number
US04888356

Reaction notes

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